CN109923147A - The manufacturing method of poly(aryl ether ketone) - Google Patents
The manufacturing method of poly(aryl ether ketone) Download PDFInfo
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- CN109923147A CN109923147A CN201880002472.7A CN201880002472A CN109923147A CN 109923147 A CN109923147 A CN 109923147A CN 201880002472 A CN201880002472 A CN 201880002472A CN 109923147 A CN109923147 A CN 109923147A
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- Prior art keywords
- manufacturing
- polycondensation
- poly
- ether ketone
- aryl ether
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 47
- 229920006260 polyaryletherketone Polymers 0.000 title claims abstract description 43
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 73
- 239000002904 solvent Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000011541 reaction mixture Substances 0.000 claims abstract description 40
- 238000001816 cooling Methods 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000010612 desalination reaction Methods 0.000 claims abstract description 30
- 230000008569 process Effects 0.000 claims abstract description 28
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 238000004064 recycling Methods 0.000 claims abstract description 8
- 238000009835 boiling Methods 0.000 claims abstract description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000010148 water-pollination Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 description 14
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 12
- 150000001339 alkali metal compounds Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- -1 compound Compound Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 239000004696 Poly ether ether ketone Substances 0.000 description 7
- 229920002530 polyetherether ketone Polymers 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical class C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920001652 poly(etherketoneketone) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- XFTIKWYXFSNCQF-UHFFFAOYSA-N N,N-dipropylformamide Chemical compound CCCN(C=O)CCC XFTIKWYXFSNCQF-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 1
- 229920004695 VICTREX™ PEEK Polymers 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/46—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00162—Controlling or regulating processes controlling the pressure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00718—Type of compounds synthesised
- B01J2219/0072—Organic compounds
- B01J2219/00736—Non-biologic macromolecules, e.g. polymeric compounds
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
Abstract
The present invention provides a kind of method of poly(aryl ether ketone) that can steadily manufacture degree of polymerization height and can be easy to recycling.It is set as including the polycondensation step for carrying out desalination polycondensation in reaction solution；And after terminating desalination polycondensation, the manufacturing method of the poly(aryl ether ketone) of cooling process is carried out to reaction mixture.At this point, polycondensation step carries out in hydrophilic solvent, under elevated pressure, the polymerization temperature in polycondensation step is set as the boiling point under the normal pressure of hydrophilic solvent or more.In addition, relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, the content of the polymer in reaction mixture when the cooling of cooling process is set as 1 mass parts or more, 50 below the mass.
Description
Technical field
The present invention relates to a kind of manufacturing methods of poly(aryl ether ketone).
Background technique
Poly(aryl ether ketone) (hereinafter also referred to as " PAEK ") is industrially generally manufactured by desalination condensation methods.It is de- at this
In salt condensation methods, generally use diphenyl sulphone (DPS) as solvent.However, diphenyl sulphone (DPS) is solid state at room temperature.Accordingly, there exist by taking off
The problem of reaction mixture that salt polycondensation obtains solidifies at room temperature.Moreover, diphenyl sulphone (DPS) is water-insoluble.Accordingly, there exist be difficult to
The problem of by the PAEK obtained by desalination condensation methods purification and recycling design.
Therefore, in order to solve the problems, various manufacturing methods are developed so far.For example, in patent document 1
In, disclose a kind of use at normal temperature for liquid and as the n-methyl-2-pyrrolidone of hydrophilic solvent (NMP) conduct
The manufacturing method of the crystallinity polyethers of reaction dissolvent.
In addition, in patent document 2, disclose a kind of hydrophilic organic amide solvent by using NMP etc and
The method for obtaining the PAEK of high molecular weight.
In addition, in patent document 3, disclose a kind of by view of can not be steady in method disclosed Patent Document 2
Surely on the basis of the PAEK for obtaining high molecular weight, the hydrophilic solvents such as solvent sulfolane and NMP are used as its improvement
Mixed solvent and the manufacturing method for manufacturing the polyethers of PAEK.
Existing technical literature
Patent document
Patent document 1: Japanese Laid-Open Patent Publication " Japanese Unexamined Patent Publication 7-138360 bulletin "
Patent document 2:WO2003/050163
Patent document 3: Japanese Laid-Open Patent Publication " Japanese Unexamined Patent Publication 2010-70657 bulletin "
Summary of the invention
Problems to be solved by the invention
However, will lead to reaction mixture in the case where method disclosed in patent document 1 and solidify at room temperature.Cause
This, needs to crush the reaction mixture after solidification by pulverizer etc. to recycle PAEK.
In addition, for method disclosed Patent Document 2, desalination polycondensation reaction in the state that polymer is precipitated into
Row.However, in method disclosed Patent Document 2, it is difficult to steadily manufacture the polymer of high molecular weight, obtained reaction
The concentration of polymer in mixture is low.
In addition, if being cooled down after the reaction, will lead to reaction in the case where method disclosed Patent Document 3
Mixture solidification.Therefore, in this case, it is also required to the reaction mixture after solidifying passing through pulverizer in order to recycle PAEK
Etc. being crushed.
The purpose of a scheme of the invention is that degree of polymerization height can steadily be manufactured and can be easy to back by providing one kind
The method of the poly(aryl ether ketone) of receipts.
Technical solution
In order to solve the above problems, the manufacturing method of the poly(aryl ether ketone) of a scheme of the invention includes: polycondensation step,
Desalination polycondensation is carried out in reaction dissolvent；And cooling process, after terminating desalination polycondensation, in the polycondensation step
Obtained reaction mixture is cooled down, and polycondensation step carries out in hydrophilic solvent, under an increased pressure, in polycondensation step
Polymerization temperature is the boiling point under the normal pressure of the hydrophilic solvent or more, relative to 100 mass parts of hydrophilic solvent, is changed with monomer
Calculate, the content of the polymer in reaction mixture when the cooling of cooling process be 1 mass parts or more 50 below the mass.
Beneficial effect
A scheme according to the present invention can steadily manufacture degree of polymerization height and can be easy to the poly(aryl ether ketone) of recycling.
Specific embodiment
Hereinafter, explaining the manufacturing method of the poly(aryl ether ketone) of an embodiment of the invention in detail (hreinafter referred to as
" this manufacturing method ").
Firstly, illustrating the polycondensation step in this manufacturing method.
<polycondensation step>
In this manufacturing method, polycondensation step refers to, the process of desalination polycondensation is carried out in reaction dissolvent.The desalination polycondensation
In the presence of alkali metal compound, Aromatic dihalide compound and aromatic dihydroxy compound is set to carry out polycondensation reaction, as a result,
It generates poly(aryl ether ketone) (PAEK).
PAEK of the invention is simultaneously not particularly restricted, as long as having by (removing from aromatic compound and should containing arlydene
Residue made of two hydrogen atoms of aromatic rings bonding) structure that is constituted with the repetitive unit of carbonyl bond and ehter bond.
It as the concrete example of such PAEK, can enumerate: polyether-ether-ketone (PEEK), polyether-ketone (PEK), polyether ketone ketone
(PEKK), polyether ether ketone ketone (PEEKK), polyetherketoneetherketoneketone (PEKEKK).
PAEK can be for example, by Japanese Laid-Open Patent Publication " examined patent publication 61-10486 bulletin ", Japanese Laid-Open Patent
Bulletin " Japanese Laid-Open Patent Publication 7-138360 bulletin ", WO2003-050163 bulletin, Japanese Laid-Open Patent Publication " special open 2010-
Documented method in No. 70657 bulletins ", Japanese Laid-Open Patent Publication " special table 2014-532109 bulletin " and obtain.
That is, by using Aromatic dihalide compound and aromatic series dihydroxy chemical combination as conventionally known starting monomer
Object, in polymer solvent, by the alkali metal of these and the alkalinity for the salt that phenates type can be formed with the aromatic dihydroxy compound
Compound, that is, alkali carbonate, alkali metal hydrogencarbonate or alkali metal hydroxide carry out desalination polycondensation together and are made
It makes.
As the Aromatic dihalide compound in polycondensation step, such as can be illustrated: 4,4 '-difluoro benzophenones, 4,4 '-
Dichloro benzophenone etc., but it is not limited to these.
As the aromatic dihydroxy compound in polycondensation step, such as can be illustrated: 1,3- dihydroxy benzenes (isophthalic two
Phenol), Isosorbide-5-Nitrae-dihydroxy benzenes (quinhydrones), 4,4 '-dihydroxybiphenyls (4,4 '-xenol), 4,4 '-dihydroxy terphenyls, 2,6- bis-
Hydroxyl naphthalene, Isosorbide-5-Nitrae-dihydroxy naphthlene, 4,4 '-dihydroxydiphenyl ethers, 4,4 '-dihydroxydiphenylsulisomers, 4,4 '-dihydroxy hexichol first
Ketone, 4,4 '-tetraphenyl bisphenols etc., but these are not limited to, in addition, the various diphenol such as bisphenol-A can be used
Class.
As the alkali metal compound in polycondensation step, the aromatic series dihydroxy that can will be used for polycondensation reaction can be enumerated
Compound is converted to the alkali metal compound of alkali metal salt.As such alkali metal compound, such as can enumerate: lithium, sodium,
The alkali carbonates such as potassium, rubidium or caesium, alkali metal hydrogencarbonate or alkali metal hydroxide etc..Among those, usually excellent
It is selected as the compound of sodium or potassium, furthermore it is preferred that for sodium or the carbonate of potassium.That is, particularly preferably sodium carbonate and potassium carbonate.It needs
Illustrate, these alkali metal compounds can not only be used only one kind, but also can according to circumstances and and with two or more, can also be with
As mixture.
The alkali metal compound used in polycondensation step from supply, reactivity from the viewpoint of and preferably have it is micro-
The solid particulate object of fine grain.Specifically, the average grain diameter of alkali metal compound is 95 μm hereinafter, preferably 5 μm~80 μm,
Further preferably 7 μm~60 μm.Particularly preferably 10 μm~30 μm.It should be noted that being averaged in the present embodiment
Partial size is the meaning of mass median diameter.The mass median diameter can be used particle analysis and is measured with analytical equipment.
In the present embodiment, it the breaking method of alkali metal compound and is not particularly limited, such as homogenizer can be passed through
Or impact grinding etc. is crushed.
In polycondensation step, the usage amount of alkali metal compound is simultaneously not particularly limited, from the viewpoint of economy etc,
Relative to 1 equivalent of hydroxyl of aromatic dihydroxy compound, the equivalent of alkali metal compound is preferably 1 or more, 2.5 hereinafter, more
Preferably 1.01 or more, 2 hereinafter, further preferably 1.02 or more, 1.5 or less.It should be noted that aromatic series dihydroxy
Either object and alkali carbonate are closed, 1 mole is equivalent to 1 equivalent, alkali metal hydrogencarbonate and alkali metal hydroxide
Each party, 2 moles are equivalent to 1 equivalent.
In addition, the usage amount of Aromatic dihalide compound and be not particularly limited, from the viewpoint of molecular weight, aromatic series
Dihalide is 0.9~1.1, preferably 0.95~1.05 relative to the molar ratio of aromatic dihydroxy compound, more preferably
0.97~1.03, further preferably 0.98~1.02.(polycondensation condition)
Then, illustrate the polycondensation condition in polycondensation step.
In this manufacturing method, polycondensation step carries out under an increased pressure in the hydrophilic solvent as reaction dissolvent.
As the concrete example of the hydrophilic solvent used in polycondensation step, preferred hydrophilic and be at room temperature liquid
Solvent.It as such solvent, such as can enumerate: n,N-Dimethylformamide (DMF), N, N- diethylformamide, N, N-
The N such as dipropyl formamide, N- dialkylformamide, n,N-dimethylacetamide, N, N- diethyl acetamide, N, N- dipropyl second
The N such as amide, N- dialkyl acetamides, n-methyl-2-pyrrolidone (NMP), N- ethyl-2-pyrrolidone, N- propyl -2- pyrroles
The N- such as alkanone, n-cyclohexyl-2-pyrrolidone alkyl -2-Pyrrolidone, N, N '-dimethyl imidazolone, N, N '-diethyl miaow
Oxazoline ketone, N, N, N '-the dialkylimidazolium quinoline ketone such as N '-dipropyl imidazolone, acyl in N- methyl caprolactam, N- ethyl hexyl
The N- alkyl caprolactams such as amine, N- propyl caprolactam, the sulfones such as sulfolane, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, two
Sulfoxides such as methyl sulfoxide, diethyl sulfoxide etc..
Moreover, as above-mentioned solvent, preferably N- alkyl -2-Pyrrolidone, N, N '-dialkylimidazolium quinoline ketone, N- alkyl
Caprolactam.Wherein, N- alkyl -2-Pyrrolidone, especially n-methyl-2-pyrrolidone is suitably used.
These hydrophilic solvents not only can be used alone, but also can be with appropriately combined two or more uses.
In this manufacturing method, the content of the monomer relative to 100 mass parts of hydrophilic solvent before desalination polycondensation is preferred
For it is more than 1 mass parts, 200 below the mass, more than more preferably 5 mass parts, 100 below the mass, further preferably 10
More than mass parts, 50 below the mass.It is higher can to manufacture the degree of polymerization within the above range for content by making monomer
PAEK。
Pressure method in polycondensation step is simultaneously not particularly limited, and is preferably more than 0MPa, 1.0MPa hereinafter, preferably in gauge pressure
0.7MPa in more preferably 0.5MPa reaction vessel below hereinafter, carry out.
In this manufacturing method, the polymerization temperature in polycondensation step is the boiling point under the normal pressure of hydrophilic solvent or more.
In this manufacturing method, from the viewpoint of obtaining high molecular weight PAEK, the polymerization temperature in polycondensation step is preferred
For 100 DEG C or more, 320 DEG C hereinafter, more preferably 150 DEG C or more, 300 DEG C hereinafter, further preferably 170 DEG C or more, 280 DEG C
Below.Polymerization temperature is temperature under an increased pressure.
In this manufacturing method, the reaction time of desalination polycondensation reaction is simultaneously not particularly limited, usually 0.1 hour or more,
10 hours hereinafter, preferably 0.5 hour or more, 7 hours hereinafter, more preferably 1 hour or more, 5 hours or less.It needs to illustrate
It is desalination polycondensation reaction or stopping heating, or adds reaction terminating agent and terminate.Reaction is in continuous situation
Under, mean residence time is set as the reaction time.
It should be noted that the mechanism of action of this manufacturing method and being not known, but can be assumed in alkali metal compound
In the presence of, for example, generating NMP ring-opening product, the NMP ring-opening product and the end PAEK in the case where using NMP as hydrophilic solvent
End carries out the side reaction of addition.
Then, illustrate the cooling process in this manufacturing method.
<cooling process>
In this manufacturing method, cooling process is to react after terminating desalination polycondensation obtained in polycondensation step
Mixture carries out cooling process.Cooling velocity when cooling down to reaction mixture is simultaneously not particularly limited, as long as example,
Reaction mixture is suitably cooled down until reaching room temperature.
When recycling reaction mixture, preferably by controlling weight ratio of the starting monomer relative to hydrophilic solvent, with slurry
Material state is recycled.
In this manufacturing method, relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, the cooling of cooling process
When reaction mixture in the content of polymer be 1 mass parts or more, 50 below the mass, more than preferably 3 mass parts, 30
Below the mass, more preferably more than 5 mass parts, 25 below the mass, it is more than particularly preferably 8 mass parts, 20 mass parts with
Under.It should be noted that in the present specification, " content relative to the polymer under the monomer conversion of hydrophilic solvent " is
Refer to, " contents of all polymer in terms of monomer conversion relative to hydrophilic solvent, as raw material ".
Relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, after terminating desalination polycondensation, implement bosher
In the case that the amount of polymer before sequence is greater than 50 mass parts, hydrophilic solvent is added in the reactive mixture, by polymer
Content adjustment within the above range.Relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, the content of polymer
In the case where less than 1 mass parts, hydrophilic solvent is removed using evaporation etc. and adjusts the content of polymer above-mentioned
In range.It is obtained by cooling by making the content of the polymer in reaction mixture while cooling within the above range
Reaction mixture at normal temperature, becomes the suspension of liquid and solid, i.e. slurry form.Thus, it is possible to be easy to carry out
The post-processing such as recycling of PAEK.It should be noted that can be used as hydrophilic solvent additional in the reactive mixture
The listed hydrophilic solvent enumerated in polycondensation step.As long as in addition, suitably setting hydrophily additional in the reactive mixture
The amount of solvent.
It is additional close in the reactive mixture after terminating desalination polycondensation, before the cooling process of implementation reaction mixture
Aqueous solvent is achieved in the solidification that can prevent reaction mixture, adjusts in reaction mixture, poly- in terms of monomer conversion
Close the effect of content of object etc.For adding the time of hydrophilic solvent in the reactive mixture, preferably opened in cooling process
Before beginning, more preferable cooling process start before precipitation PAEK before.
It should be noted that comprising solvent, by-product salt and containing PAEK in the reaction mixture for becoming slurry form
Reaction mixture.
By the reduced viscosity of the obtained PAEK of this manufacturing method be 0.15~1.5 very it is high.In this specification
In, high polymerization degree refers to, a height of synonymous with reduced viscosity.Therefore, according to this manufacturing method, high polymerization degree can be stably obtained
PAEK.Moreover, the reaction mixture containing PAEK is the slurry with mobility under room temperature (25 DEG C) according to this manufacturing method
State.Thus, it is easy to convey reaction mixture.Moreover, this manufacturing method may include recovery process described below.
<recovery process>
Recovery process in this manufacturing method refers to, to the work recycled by the obtained reaction mixture of cooling process
Sequence.According to this manufacturing method, as described above, since reaction mixture is the slurry form with mobility at normal temperature, because
This may be easy to recycling reaction mixture.
In addition, further, this manufacturing method also may include separation described below other than including recovery process
Process.
<separation process>
Separation process in this manufacturing method refers to, after recovery process, by reaction mixture be separated into polymerizate and
The process of solvent.The separation method of reaction mixture is simultaneously not particularly limited, such as described hydrophilic by utilizing reaction mixture
Alcohol, the acetone such as property solvent, water, inorganic acid aqueous solution, methanol, ethyl alcohol etc. and their combination are cleaned, and are carried out with filter paper etc.
It is separated by solid-liquid separation to carry out.Thus, it is possible to which the solvent purifications after separation are recycled.
The manufacturing method of the PAEK of present embodiment can be in intermittent, semibatch, continous way and their combination
Any method.
The manufacturing method of the poly(aryl ether ketone) of a scheme of the invention includes: polycondensation step, is taken off in reaction dissolvent
Salt polycondensation；And cooling process cools down reaction mixture, polycondensation step is in hydrophily after terminating desalination polycondensation
In solvent, under an increased pressure carry out, the polymerization temperature in polycondensation step be the boiling point under the normal pressure of the hydrophilic solvent with
On, it is poly- in the reaction mixture when cooling of cooling process in terms of monomer conversion relative to 100 mass parts of hydrophilic solvent
Close object content be 1 mass parts or more 50 below the mass.
[summary]
The manufacturing method of the poly(aryl ether ketone) of a scheme of the invention includes: polycondensation step, is carried out in reaction dissolvent
Desalination polycondensation；And cooling process, after terminating desalination polycondensation, to the reaction mixture obtained in the polycondensation step
It is cooled down, polycondensation step carries out in hydrophilic solvent, under an increased pressure, and the polymerization temperature in polycondensation step is the parent
More than the boiling point under the normal pressure of aqueous solvent, relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, cooling process
The content of the polymer in reaction mixture when cooling be 1 mass parts or more 50 below the mass.
In a scheme of the invention, preferably, polycondensation step is more than that 0MPa, 1.0MPa reaction below are held in gauge pressure
It is carried out in device.
In addition, preferably, the polymerization temperature in polycondensation step is 100 DEG C or more, 320 in a scheme of the invention
DEG C or less.
Further, in a scheme of the invention, preferably, relative to 100 mass parts of hydrophilic solvent, desalination polycondensation
The content of preceding monomer be 1 mass parts or more 200 below the mass.
Further, in a scheme of the invention, preferably, comprising: after terminating desalination polycondensation, implementing to cool down
Before process, the process of hydrophilic solvent is added in the reactive mixture.
It further, further comprise recovery process, to by cooling process preferably in a scheme of the invention
Obtained reaction mixture is recycled.
Further, in a scheme of the invention, preferably, including separation process will react after recovery process
Mixture is separated into polymerizate and solvent.
Further, in a scheme of the invention, preferably, hydrophilic solvent is n-methyl-2-pyrrolidone.
In the following, embodiment is shown, illustrates embodiments of the present invention in further detail.Certainly, the present invention is not
It is defined in embodiment below, can be self-evident for various schemes for detail section.Further, the present invention and unlimited
It due to above embodiment, can be made various changes in the range shown in claim, disclosed technical solution respectively is fitted
The embodiment obtained from combination is also included in the technical scope of the present invention.In addition, documented all in this specification
Document is cited as reference.
[embodiment]
(embodiment 1)
In the potassium carbonate (K as alkali metal compound2CO3) in the presence of, in n-methyl-2-pyrrolidone (NMP),
4,4 '-difluoro benzophenone (DFBP) 22.038g and quinhydrones (HQ) 11.011g as aromatic dihydroxy compound are carried out
Desalination polycondensation.After desalination polycondensation reaction, reactant is cooled to room temperature.Reactant after cooling is slurry at room temperature
Shape.It should be noted that condition when desalination polycondensation is as described below.
Reaction system concentration: (DFBP+HQ)/NMP (100 mass parts)=20 mass parts
Molar ratio: DFBP/HQ=1.01
K2CO3/ HQ=1.1
Polymerization time: after 180 DEG C were polymerize with 0.5 hour, then, it was polymerize at 260 DEG C with 1.0 hours.
Polymerization pressure: 0.3MPaG
The reaction mixture of the pulp-like obtained by desalination polycondensation reaction is cleaned with water and methanol, with filter paper (5A)
It is separated by solid-liquid separation.For obtained solid component, reduced viscosity measurement and fusing point test have been carried out.It is obtained solid
The PEEK that the reduced viscosity of body ingredient is 0.42 (dL/g), fusing point is 336 DEG C.It should be noted that the measurement of reduced viscosity and
The fusing point test progress by following so respectively.
<production of sample solution>
Solid component 0.1g and 4- the chlorophenol 10mL obtained as described so is packed into pressure-resistant screw socket bottle (screw
Vial it in), stirs in 180 DEG C of oil bath, heats 20 minutes on one side on one side, solid component dissolution has been obtained into solution.It connects
, obtained solution is let cool until room temperature, later, solution 3mL o-dichlorohenzene 7mL is diluted and sample is made
Solution.
<measurement of reduced viscosity>
The sample solution obtained as described so is filtered with filter paper (No.7), at 35 DEG C with Ubbelohde viscometer into
Measurement is gone.
<measurement of fusing point>
Using differential scanning calorimetry measurement device (TA Instruments manufactures DSC Q100), the progress by following.
That is, obtained sample 3mg is put into aluminium crucible, with 20 DEG C/min, under conditions of being passed through nitrogen (50ml/ minutes) from
30 DEG C are heated to 400 DEG C, determine fusing point.(embodiment 2)
In addition to the reaction system concentration in embodiment 1 is changed to it is following in this way other than, similarly to Example 1 carry out
Desalination polycondensation.
Reaction system concentration: (DFBP+HQ)/NMP (100 mass parts)=30 mass parts
After terminating desalination polycondensation reaction, NMP220.328g is added in the reactive mixture, and later, reaction is mixed
Object is cooled down.
After cooling, reaction mixture is cooled to room temperature.Reaction mixture after cooling becomes pulp-like at room temperature.
Then, similarly to Example 1, the reaction mixture of pulp-like is separated by solid-liquid separation, to obtained solid
The reduced viscosity and fusing point of ingredient are determined.Reduced viscosity for obtained solid component is 1.29 (dL/g), fusing point
For 336 DEG C of PEEK.
(embodiment 3)
The sample for changing the blending ratio of NMP and PEEK (Victrex company manufacture 450P reduced viscosity 1.18) is put
Enter in pressure-resistant crucible, with 20 DEG C/min, under conditions of being passed through nitrogen (50ml/ minutes), carries out twice from 30 DEG C to 400 DEG C
Heating/cooling.The fusing point of the sample as obtained from the result of secondary heating/cooling, decrease temperature crystalline temperature such as institute in table 1
Show.It should be noted that the measurement of fusing point and decrease temperature crystalline temperature has used differential scanning calorimetry measurement device (TA
Instruments manufactures DSC Q100).
[table 1]
Tm: fusing point
Tc: decrease temperature crystalline temperature
Known to according to the result of table 1: in embodiment 1 and 2, polymerization temperature is 202 DEG C of boiling point or more of NMP, and is
PEEK is in the temperature range of dissolved state.
Industrial utilizability
Poly(aryl ether ketone) of the invention can be used as the former material in the various fields such as automobile, precision equipment as engineering resin
Material.
Claims (8)
1. a kind of manufacturing method of poly(aryl ether ketone) comprising:
Polycondensation step carries out desalination polycondensation in reaction dissolvent；And
Cooling process carries out the reaction mixture obtained in the polycondensation step after terminating the desalination polycondensation
It is cooling,
The polycondensation step carries out in hydrophilic solvent, under an increased pressure,
Polymerization temperature in the polycondensation step is the boiling point under the normal pressure of the hydrophilic solvent or more,
The reaction relative to 100 mass parts of hydrophilic solvent, in terms of monomer conversion, when the cooling of the cooling process
The content of polymer in mixture is 1 mass parts or more, 50 below the mass.
2. the manufacturing method of poly(aryl ether ketone) according to claim 1, wherein the polycondensation step gauge pressure be more than 0MPa,
It is carried out in 1.0MPa reaction vessel below.
3. the manufacturing method of poly(aryl ether ketone) according to claim 1 or 2, wherein the polymerization temperature in the polycondensation step
It is 100 DEG C or more, 320 DEG C or less.
4. the manufacturing method of poly(aryl ether ketone) described in any one of claim 1 to 3, wherein relative to the hydrophily
100 mass parts of solvent, the content of the monomer before the desalination polycondensation be 1 mass parts or more, 200 below the mass.
5. the manufacturing method of poly(aryl ether ketone) according to any one of claims 1 to 4, wherein include: to terminate described take off
After salt polycondensation, before implementing the cooling process, the process of additional hydrophilic solvent in the reaction mixture.
6. the manufacturing method of poly(aryl ether ketone) according to any one of claims 1 to 5, wherein further comprise recycling work
Sequence recycles the reaction mixture obtained by the cooling process.
7. the manufacturing method of poly(aryl ether ketone) according to claim 6, wherein including separation process, in the recycling work
After sequence, the reaction mixture is separated into polymerizate and solvent.
8. the manufacturing method of poly(aryl ether ketone) according to any one of claims 1 to 7, wherein the hydrophilic solvent is
N-methyl-2-pyrrolidone.
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| JP2017198718 | 2017-10-12 | ||
| JP2017-198718 | 2017-10-12 | ||
| PCT/JP2018/037917 WO2019074056A1 (en) | 2017-10-12 | 2018-10-11 | Polyaryletherketone production method |
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| US (1) | US11485821B2 (en) |
| EP (1) | EP3517562A4 (en) |
| JP (2) | JP6749418B2 (en) |
| KR (1) | KR102160404B1 (en) |
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| CN114051508A (en) * | 2019-07-24 | 2022-02-15 | Dic株式会社 | Polyaryletherketone resin, method for producing same, and molded article |
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| CN113563576A (en) * | 2021-07-26 | 2021-10-29 | 中国科学院长春应用化学研究所 | Method for rapidly preparing tertiary amine polymer |
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| JP4517272B2 (en) * | 2002-01-24 | 2010-08-04 | 東洋紡績株式会社 | Photocrosslinkable polymer solid electrolyte, cross-linked polymer solid electrolyte membrane and method for producing the same |
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- 2018-10-11 KR KR1020187036335A patent/KR102160404B1/en active IP Right Grant
- 2018-10-11 WO PCT/JP2018/037917 patent/WO2019074056A1/en unknown
- 2018-10-11 CN CN201880002472.7A patent/CN109923147B/en not_active Expired - Fee Related
- 2018-10-11 JP JP2018558359A patent/JP6749418B2/en not_active Expired - Fee Related
- 2018-10-11 EP EP18819255.3A patent/EP3517562A4/en not_active Withdrawn
- 2018-10-11 US US16/314,537 patent/US11485821B2/en active Active
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| JPH07138360A (en) * | 1993-11-17 | 1995-05-30 | Idemitsu Material Kk | Production of crystalline polyether |
| JP2006111664A (en) * | 2004-10-12 | 2006-04-27 | Toyobo Co Ltd | Method for producing polyarylene-based polymer |
| CN101186695A (en) * | 2007-11-15 | 2008-05-28 | 吉林大学 | Soluble fluorine-containing polyaryl ether ketone high-performance material, preparation method thereof and mixed film of the same and epoxy resin |
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| JP6749418B2 (en) | 2020-09-02 |
| CN109923147B (en) | 2022-04-01 |
| KR20190041968A (en) | 2019-04-23 |
| US20200399425A1 (en) | 2020-12-24 |
| US11485821B2 (en) | 2022-11-01 |
| JPWO2019074056A1 (en) | 2019-11-14 |
| JP2020094228A (en) | 2020-06-18 |
| WO2019074056A1 (en) | 2019-04-18 |
| KR102160404B1 (en) | 2020-09-28 |
| EP3517562A4 (en) | 2020-02-12 |
| EP3517562A1 (en) | 2019-07-31 |
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